The objective of this research is to develop a total synthesis of the antitumor antibiotic streptonigrin. In this proposal we describe and evaluate eight general approaches to this cytotoxic metabolite which deserve experimental investigation. They are designed to allow the utilization of some of the same starting materials in the study of multiple, distinct pathways of synthesis. However, all of the routes have in common the act that they involve making the pyridine ring as the convergent step. This strategy should make it possible to synthesize a variety of analogs of streptonigrin of value in the investigation of pharmacological structure-activity relationships.